10 Star Trek Undercover Operations That Went Wrong

After years of Star Trek adventures, we've grown accustomed to the idea that Starfleet officers are the best of the best. Until, one day, they're sent on a covert operation and everything unravels. And frankly, there are so many disastrous undercover missions on Starfleet's books at this point that it was a struggle narrowing it down to just ten.

We blame James Bond and Ethan Hunt for making it look so easy. Sort of. To be fair, mission-almost-impossible suits some of our favourite Fleeters better than others...and some even take to subterfuge and skulduggery like a whale to 23rd-century water.

Looking at you, Sisko.

But on the whole, whenever an episode opens with carefully laid plans for infiltration, disguise or sabotage, we just know that something will go wrong along the way. Blown covers, cultural contamination...even missing communicators, there are a hundred and one ways a mission can fall apart.

Maybe the plan was based on rotten intel. Or it was just a bad idea from the start. And let's face it, sometimes the person they send, for all their brilliance in their own field, just isn't suited to the world of spycraft.

There is one very important lesson we can learn from all this, though: if you want an espionage plot to go well, you just need a Garak at your back.

You know exactly what we're talking about. Stardust City Rag in Star Trek: Picard.

We just have to come out and say it. Who looked at Picard wearing that eyepatch and beret, heard his ridiculous French accent and said, 'yeah, that has undercover mission success written all over it'?

Seriously, someone on La Sirena should have known better and sent Picard to timeout to think about what he'd done. There was no way in the galaxy that his disguise should have worked. No matter what Raffi injected them with to fool the alien on Freecloud that can literally sniff out lies.

The strangest part is, it's not even this terrible disguise that messes up the mission. The plan was simple. Retrieve Maddox from Bjayzl by having Rios pose as a facer on Freecloud, offer the highly valuable Seven of Nine as a trade, then transport to safety.

What they didn't know was that Seven manipulated the entire situation to get close to Bjayzl, seeking vengeance for the murder of Icheb. When Seven's ulterior motive is revealed, the situation devolves into a chaotic standoff that puts them all in danger. And while Seven plays along with a deal that allows them to leave peacefully, she later returns alone to claim Bjayzl's life.

It's fair to say that Stardust City Rag is a prime example of streaming Trek's penchant for tonal whiplash, but even so, we still maintain that Monsieur Eyepatch should never have been allowed to beam down in the first place.